6062-24-4

Basic information

• Product Name: 1-Methyl-5-hydroxy-2-indolinone
• Synonyms: 1-Methyl-5-hydroxy-2-indolinone;5-hydroxy-1-methylindolin-2-one;1,3-Dihydro-5-Hydroxy-1-Methyl-2H-Indol-2-One;2H-Indol-2-one, 1,3-dihydro-5-hydroxy-1-methyl-;1,3-Dihydro-5-Hydroxy-1-Methyl-2H-Indol-2-One(WX649015)
• CAS NO: 6062-24-4
• Molecular Formula: C9H9NO2
• Molecular Weight: 163.17326
• Mol File: 6062-24-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Methyl-5-hydroxy-2-indolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-5-hydroxy-2-indolinone(6062-24-4)
• EPA Substance Registry System: 1-Methyl-5-hydroxy-2-indolinone(6062-24-4)

Safety Data

• Hazardous Substances Data: 6062-24-4(Hazardous Substances Data)

Usage

Chemical structure

A derivative of indole

Usage

Building block in the synthesis of pharmaceuticals and organic compounds

Medicinal properties

Potential as an inhibitor of various enzymes and proteins

Anticancer properties

Ability to inhibit the growth of cancer cells

Versatility

Potential applications in medicine, drug discovery, and organic synthesis.

Upstream product

• 86735-53-7 2-methyl-4-methoxy-N-methylaniline 
• 150-75-4 N-methyl-p-aminophenol 
• 2567-80-8 chloro-acetic acid-(4-hydroxy-N-methyl-anilide) 
• 7699-22-1 5-methoxy-1-methylindolin-2-one 
• 63031-64-1 2-chloro-N-(4-methoxy-phenyl)-N-methylacetamide 
• 3154-18-5 N-methyl-p-phenetidine 
• 6118-92-9 N-(4-hydroxy-phenyl)-N-methyl-glycine 

Downstream Products

• 1443787-60-7 C₁₉H₁₉NO₅ 
• 851681-89-5 Oxindole 
• 851682-14-9 5-methyl-3,6-dioxo-2,3,6,7-tetrahydro-furo[2,3-f]indole 
• 851682-16-1 5-methyl-6-oxo-6,7-dihydro-furo[2,3-f]indole 
• 111412-78-3 3-(4-diethylamino-phenylimino)-5-hydroxy-1-methyl-indolin-2-one 
• 158719-19-8 2,2'-dithiobis [N-phenyl-5-acetoxy-1-methylindolyl-3-carboxamide] 
• 1027507-85-2 Acetic acid 1-methyl-3-phenylcarbamoyl-2-thioxo-2,3-dihydro-1H-indol-5-yl ester 

Relevant articles and documents

A new chemical tool for exploring the physiological function of the PDE2 isozyme

Oxindole (2) is a potent and selective PDE2 inhibitor with a favorable ADME, physiochemical and pharmacokinetic profile to allow for use as a chemical tool in elucidating the physiological role of PDE2.

Tyrosine kinase inhibitors. 3. Structure-activity relationships for inhibition of protein tyrosine kinases by nuclear-substituted derivatives of 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)

A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H- indole-3-carboxamides) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3- dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity. While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20- fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC50s in the range 2-25 μM, the most active being 4- substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF- mediated phosphorylation.